Electrochemical, Spectroscopic, and 1 O 2 Sensitization Characteristics of 10,10-Dimethylbiladiene Complexes of Zinc and Copper

Pistner, Allen J.; Pupillo, Rachel C.; Yap, Glenn P. A.; Lutterman, Daniel A.; Ma, Ying-Zhong; Rosenthal, Joel

doi:10.1021/jp506412r

Title: Electrochemical, Spectroscopic, and ¹ O ₂ Sensitization Characteristics of 10,10-Dimethylbiladiene Complexes of Zinc and Copper

Journal Article · Tue Oct 07 00:00:00 EDT 2014 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/jp506412r· OSTI ID:1163878

Pistner, Allen J. ^[1]; Pupillo, Rachel C. ^[1]; Yap, Glenn P. A. ^[1]; Lutterman, Daniel A. ^[2]; Ma, Ying-Zhong ^[2]; Rosenthal, Joel ^[1]

Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States
Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37831, United States

The synthesis, electrochemistry and photophysical characterization of a 10,10- dimethylbiladiene tetrapyrrole bearing ancillary pentafluorophenyl groups at the 5 and 15-meso positions (DMBil1) is presented. This non-macrocyclic tetrapyrrole platform is robust and can serve as an excellent ligand scaffold for Zn²⁺ and Cu²⁺ centers. X-ray diffraction studies conducted for DMBil1 along with the corresponding Zn[DMBil1] and Cu[DMBil1] complexes show that this ligand scaffold binds a single metal ion within the tetrapyrrole core. Additionally, electrochemical experiments revealed that all three of the aforementioned compounds display an interesting redox chemistry, as the DMBil1 framework can be both oxidized and reduced by two electrons. Spectroscopic and photophysical experiments carried out for DMBil1, Zn[DMBil1] and Cu[DMBil1] provide a basic picture of the electronic properties of these platforms. All three biladiene derivatives strongly absorb light in the visible region and are weakly emissive. The ability of these compounds to sensitize the formation of ¹O₂ at wavelengths longer than 500 nm was probed. Both the freebase and Zn²⁺ 10,10-dimethylbiladiene architectures show modest efficiencies for ¹O₂ sensitization. The combination of structural, electrochemical and photophysical data detailed herein, provides a basis for the design of additional biladiene constructs for the activation of O₂ and other small molecules.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1163878

Alternate ID(s):: OSTI ID: 1185659

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Vol. 118 Journal Issue: 45; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 17 works

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